Methane → HCID 19009432, compound

HRID 1741990Notes

Reaction equation

HRID 1741990 reaction equation
[CH3:1][C:2]1O[CH:7]=[CH:6][C:4](=[O:5])[C:3]=1[OH:9].[CH2:10]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:12][CH3:13].C>O>[CH2:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH:7]=[CH:6][C:4](=[O:5])[C:3]([OH:9])=[C:2]1[CH3:1])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 297MethaneHCID 8369MaltolHCID 854611-Propanamine, 3-butoxy-

Product 1

HCID 19009432HCID 19009432, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(3-Butoxypropyl)-3-hydroxy-2-methylpyrid-4-one was prepared by dissolving 10.0 g maltol and 3 equivalents of 3-butoxypropylamine in 200 ml of water. The mixture was refluxed for 72 hours, decolorizing charcoal was added and the mixture was stirred for an additional 0.5 hours. The mixture was filtered through a coarse frit containing 0.5 inches of Celite, and the filtrate was concentrated in vacuo to remove the water and excess amine. The remaining oil was crystallized from ether, yielding crystals of pure product.

Workup

  1. temperatureThe mixture was refluxed for 72 hours
  2. additionwas added
  3. filtrationThe mixture was filtered through a coarse frit
  4. additioncontaining 0.5 inches of Celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto remove the water and excess amine
  7. customThe remaining oil was crystallized from ether
  8. customyielding crystals of pure product

Sources & evidence

ORD record
ord-a6da0e5874064acbb1a0fd06842a915d
Source dataset
uspto-grants-1994_08
Patent number
US05336482

Reaction notes

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